# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_RajanBabu1696 _audit_creation_date 2013-08-02T16:24:17-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'RajanBabu 1696' _chemical_formula_moiety 'C21 H17 N5 O3' _chemical_formula_sum 'C21 H17 N5 O3' _chemical_formula_weight 387.4 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system orthorhombic _space_group_name_H-M_alt P212121 _space_group_name_Hall 'P 2ac 2ab' _space_group_IT_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.1209(1) _cell_length_b 13.4823(2) _cell_length_c 26.8004(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1850.34(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1950 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'very thin rod' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_special_details ;All work was done at 150 K using an Oxford Cryosystems Cryostream Cooler. The data collection strategy was set up to measure a quadrant of reciprocal space with a redundancy factor of 3.1, which means that 90% of these reflections were measured at least 3.1 times. Phi and omega scans with a frame width of 1.0 degree were used. Data integration was done with Denzo, and scaling and merging of the data was done with Scalepack. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.902 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.12723 _diffrn_orient_matrix_ub_12 -0.146274 _diffrn_orient_matrix_ub_13 -0.234536E-1 _diffrn_orient_matrix_ub_21 -0.19904E-2 _diffrn_orient_matrix_ub_22 0.100474E-1 _diffrn_orient_matrix_ub_23 -0.734607E-1 _diffrn_orient_matrix_ub_31 0.282886E-1 _diffrn_orient_matrix_ub_32 0.241979E-1 _diffrn_orient_matrix_ub_33 0.25431E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.058 _diffrn_reflns_av_unetI/netI ? _diffrn_reflns_number 21672 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 3249 _reflns_number_gt 2588 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ;The hydrogen atom bonded to atom N(4) was located on a difference electron density map and refined isotropically. The rest of the hydrogen atoms were included in the model at calculated positions using a riding model with U(H) = 1.2*Ueq(bonded atom). Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0327P)^2^+0.0133P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3249 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.0712 _refine_ls_wR_factor_gt 0.065 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_diff_density_max 0.175 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.036 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1697(4) 0.73912(13) 0.18731(6) 0.0219(4) Uani 1 1 d . . . H1 H 0.3537 0.7569 0.1785 0.026 Uiso 1 1 calc R . . C2 C -0.0081(4) 0.82389(12) 0.16811(6) 0.0242(4) Uani 1 1 d . . . H2 H -0.1945 0.8019 0.1692 0.029 Uiso 1 1 calc R . . C3 C 0.0642(4) 0.85109(14) 0.11498(7) 0.0246(5) Uani 1 1 d . . . C4 C 0.2815(4) 0.90915(14) 0.10540(8) 0.0332(5) Uani 1 1 d . . . H4 H 0.3831 0.9335 0.1324 0.04 Uiso 1 1 calc R . . C5 C 0.3527(4) 0.93215(15) 0.05680(8) 0.0404(6) Uani 1 1 d . . . H5 H 0.5025 0.9719 0.0507 0.048 Uiso 1 1 calc R . . C6 C 0.2064(4) 0.89737(16) 0.01744(8) 0.0403(6) Uani 1 1 d . . . H6 H 0.2546 0.9134 -0.0158 0.048 Uiso 1 1 calc R . . C7 C -0.0088(4) 0.83954(15) 0.02630(7) 0.0404(6) Uani 1 1 d . . . H7 H -0.1101 0.8155 -0.0008 0.048 Uiso 1 1 calc R . . C8 C -0.0789(4) 0.81602(15) 0.07495(7) 0.0330(5) Uani 1 1 d . . . H8 H -0.2272 0.7753 0.0808 0.04 Uiso 1 1 calc R . . C9 C 0.1065(4) 0.64183(13) 0.16119(6) 0.0230(4) Uani 1 1 d . . . C10 C 0.2538(4) 0.61071(15) 0.12072(7) 0.0329(5) Uani 1 1 d . . . H10 H 0.3961 0.65 0.1095 0.039 Uiso 1 1 calc R . . C11 C 0.1949(5) 0.52249(15) 0.09646(8) 0.0410(6) Uani 1 1 d . . . H11 H 0.2966 0.502 0.0687 0.049 Uiso 1 1 calc R . . C12 C -0.0097(4) 0.46473(15) 0.11242(7) 0.0393(6) Uani 1 1 d . . . H12 H -0.05 0.4044 0.0958 0.047 Uiso 1 1 calc R . . C13 C -0.1556(4) 0.49490(15) 0.15268(8) 0.0390(6) Uani 1 1 d . . . H13 H -0.2959 0.4548 0.1641 0.047 Uiso 1 1 calc R . . C14 C -0.1003(4) 0.58293(14) 0.17664(7) 0.0335(5) Uani 1 1 d . . . H14 H -0.2049 0.6035 0.204 0.04 Uiso 1 1 calc R . . C15 C 0.3684(4) 0.72914(13) 0.27006(6) 0.0209(4) Uani 1 1 d . . . C16 C 0.3290(4) 0.71259(12) 0.32460(6) 0.0209(4) Uani 1 1 d . . . C17 C 0.1311(4) 0.65211(13) 0.34304(6) 0.0263(5) Uani 1 1 d . . . H17 H 0.0073 0.624 0.3207 0.032 Uiso 1 1 calc R . . C18 C 0.1133(4) 0.63254(13) 0.39359(7) 0.0277(5) Uani 1 1 d . . . H18 H -0.0206 0.5909 0.4064 0.033 Uiso 1 1 calc R . . C19 C 0.2951(4) 0.67502(14) 0.42494(6) 0.0235(4) Uani 1 1 d . . . C20 C 0.4917(4) 0.73635(13) 0.40832(6) 0.0264(5) Uani 1 1 d . . . H20 H 0.6121 0.7654 0.431 0.032 Uiso 1 1 calc R . . C21 C 0.5084(4) 0.75445(13) 0.35759(6) 0.0252(4) Uani 1 1 d . . . H21 H 0.6436 0.7958 0.3451 0.03 Uiso 1 1 calc R . . N1 N 0.0265(3) 0.91234(12) 0.20087(6) 0.0336(4) Uani 1 1 d . . . N2 N -0.1721(4) 0.93971(13) 0.22299(6) 0.0391(5) Uani 1 1 d . . . N3 N -0.3386(5) 0.97430(16) 0.24475(8) 0.0700(7) Uani 1 1 d . . . N4 N 0.1565(3) 0.72997(12) 0.24133(6) 0.0244(4) Uani 1 1 d . . . H1N4 H 0.018(4) 0.7281(13) 0.2536(6) 0.019(6) Uiso 1 1 d . . . N5 N 0.2802(4) 0.65126(12) 0.47864(6) 0.0309(4) Uani 1 1 d . . . O1 O 0.5919(2) 0.74071(10) 0.25332(4) 0.0283(3) Uani 1 1 d . . . O2 O 0.4591(3) 0.67886(10) 0.50579(5) 0.0395(4) Uani 1 1 d . . . O3 O 0.0897(3) 0.60441(10) 0.49343(5) 0.0430(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0164(10) 0.0300(11) 0.0193(10) 0.0001(8) 0.0011(8) -0.0008(10) C2 0.0194(10) 0.0248(10) 0.0283(10) -0.0030(9) -0.0004(9) -0.0043(9) C3 0.0195(11) 0.0227(10) 0.0315(11) 0.0042(9) 0.0033(9) 0.0048(9) C4 0.0303(12) 0.0287(12) 0.0406(13) 0.0057(10) 0.0013(11) 0.0009(10) C5 0.0335(13) 0.0309(13) 0.0567(15) 0.0119(11) 0.0126(12) -0.0011(11) C6 0.0458(14) 0.0388(13) 0.0363(13) 0.0130(11) 0.0114(12) 0.0118(12) C7 0.0416(14) 0.0490(14) 0.0306(12) 0.0039(11) -0.0004(11) -0.0017(13) C8 0.0272(12) 0.0374(12) 0.0343(12) 0.0054(10) 0.0008(11) -0.0022(10) C9 0.0202(10) 0.0281(11) 0.0206(10) 0.0006(8) -0.0027(9) 0.0034(9) C10 0.0340(13) 0.0357(13) 0.0289(12) -0.0004(10) 0.0048(10) -0.0001(10) C11 0.0489(16) 0.0451(14) 0.0289(12) -0.0094(11) 0.0081(12) 0.0062(13) C12 0.0450(14) 0.0325(13) 0.0404(13) -0.0101(11) -0.0044(12) 0.0020(13) C13 0.0375(13) 0.0297(12) 0.0497(14) -0.0091(10) 0.0031(13) -0.0057(11) C14 0.0290(12) 0.0360(12) 0.0354(12) -0.0041(10) 0.0077(10) 0.0002(11) C15 0.0181(11) 0.0212(11) 0.0235(10) -0.0022(8) -0.0004(9) -0.0014(9) C16 0.0177(10) 0.0229(10) 0.0221(10) -0.0036(8) 0.0027(9) 0.0027(9) C17 0.0233(11) 0.0293(11) 0.0262(11) -0.0021(9) -0.0011(10) -0.0013(10) C18 0.0269(11) 0.0289(12) 0.0272(12) 0.0033(9) 0.0042(10) -0.0036(10) C19 0.0280(11) 0.0239(11) 0.0185(10) -0.0005(9) 0.0015(9) 0.0045(10) C20 0.0236(11) 0.0311(11) 0.0245(11) -0.0033(9) -0.0046(9) -0.0007(11) C21 0.0200(11) 0.0302(11) 0.0253(11) -0.0018(9) 0.0008(9) -0.0032(11) N1 0.0270(10) 0.0316(10) 0.0421(10) -0.0090(8) 0.0059(9) 0.0008(9) N2 0.0469(13) 0.0319(11) 0.0385(11) -0.0078(8) 0.0054(11) -0.0079(10) N3 0.0640(16) 0.0590(14) 0.0871(17) -0.0378(13) 0.0365(14) -0.0152(13) N4 0.0138(10) 0.0389(11) 0.0206(9) -0.0018(7) 0.0039(8) -0.0018(9) N5 0.0411(11) 0.0270(10) 0.0244(10) 0.0014(8) 0.0007(9) 0.0029(9) O1 0.0174(8) 0.0423(8) 0.0253(7) -0.0002(6) 0.0017(6) -0.0025(7) O2 0.0420(9) 0.0507(9) 0.0258(7) 0.0017(7) -0.0086(8) -0.0006(8) O3 0.0570(11) 0.0403(9) 0.0317(8) 0.0076(7) 0.0050(8) -0.0158(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N4 1.455(2) . ? C1 C9 1.522(2) . ? C1 C2 1.549(2) . ? C1 H1 1 . ? C2 N1 1.491(2) . ? C2 C3 1.516(2) . ? C2 H2 1 . ? C3 C8 1.382(2) . ? C3 C4 1.385(3) . ? C4 C5 1.388(3) . ? C4 H4 0.95 . ? C5 C6 1.376(3) . ? C5 H5 0.95 . ? C6 C7 1.371(3) . ? C6 H6 0.95 . ? C7 C8 1.389(3) . ? C7 H7 0.95 . ? C8 H8 0.95 . ? C9 C10 1.386(2) . ? C9 C14 1.387(2) . ? C10 C11 1.389(3) . ? C10 H10 0.95 . ? C11 C12 1.374(3) . ? C11 H11 0.95 . ? C12 C13 1.374(3) . ? C12 H12 0.95 . ? C13 C14 1.379(3) . ? C13 H13 0.95 . ? C14 H14 0.95 . ? C15 O1 1.239(2) . ? C15 N4 1.331(2) . ? C15 C16 1.492(2) . ? C16 C17 1.391(2) . ? C16 C21 1.395(2) . ? C17 C18 1.383(2) . ? C17 H17 0.95 . ? C18 C19 1.379(2) . ? C18 H18 0.95 . ? C19 C20 1.377(3) . ? C19 N5 1.476(2) . ? C20 C21 1.384(2) . ? C20 H20 0.95 . ? C21 H21 0.95 . ? N1 N2 1.234(2) . ? N2 N3 1.133(2) . ? N4 H1N4 0.783(19) . ? N5 O2 1.228(2) . ? N5 O3 1.2278(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 C1 C9 112.02(14) . . ? N4 C1 C2 111.44(14) . . ? C9 C1 C2 110.98(13) . . ? N4 C1 H1 107.4 . . ? C9 C1 H1 107.4 . . ? C2 C1 H1 107.4 . . ? N1 C2 C3 109.30(15) . . ? N1 C2 C1 108.94(14) . . ? C3 C2 C1 110.28(14) . . ? N1 C2 H2 109.4 . . ? C3 C2 H2 109.4 . . ? C1 C2 H2 109.4 . . ? C8 C3 C4 118.38(18) . . ? C8 C3 C2 121.10(17) . . ? C4 C3 C2 120.48(17) . . ? C3 C4 C5 120.8(2) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 120.0(2) . . ? C6 C5 H5 120 . . ? C4 C5 H5 120 . . ? C7 C6 C5 119.92(19) . . ? C7 C6 H6 120 . . ? C5 C6 H6 120 . . ? C6 C7 C8 120.0(2) . . ? C6 C7 H7 120 . . ? C8 C7 H7 120 . . ? C3 C8 C7 120.90(19) . . ? C3 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C10 C9 C14 118.41(17) . . ? C10 C9 C1 120.34(17) . . ? C14 C9 C1 121.25(16) . . ? C9 C10 C11 120.5(2) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 120.4(2) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 119.43(19) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C12 C13 C14 120.6(2) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C13 C14 C9 120.72(19) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? O1 C15 N4 122.87(16) . . ? O1 C15 C16 119.90(16) . . ? N4 C15 C16 117.23(16) . . ? C17 C16 C21 119.44(16) . . ? C17 C16 C15 122.29(16) . . ? C21 C16 C15 118.13(16) . . ? C18 C17 C16 120.51(17) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C19 C18 C17 118.24(18) . . ? C19 C18 H18 120.9 . . ? C17 C18 H18 120.9 . . ? C20 C19 C18 123.08(16) . . ? C20 C19 N5 118.93(17) . . ? C18 C19 N5 117.97(18) . . ? C19 C20 C21 117.98(17) . . ? C19 C20 H20 121 . . ? C21 C20 H20 121 . . ? C20 C21 C16 120.72(17) . . ? C20 C21 H21 119.6 . . ? C16 C21 H21 119.6 . . ? N2 N1 C2 115.10(16) . . ? N3 N2 N1 172.1(2) . . ? C15 N4 C1 122.58(17) . . ? C15 N4 H1N4 119.8(13) . . ? C1 N4 H1N4 117.6(13) . . ? O2 N5 O3 123.88(16) . . ? O2 N5 C19 118.24(17) . . ? O3 N5 C19 117.88(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 C1 C2 N1 44.2(2) . . . . ? C9 C1 C2 N1 169.78(14) . . . . ? N4 C1 C2 C3 164.15(15) . . . . ? C9 C1 C2 C3 -70.26(18) . . . . ? N1 C2 C3 C8 -140.37(18) . . . . ? C1 C2 C3 C8 99.9(2) . . . . ? N1 C2 C3 C4 41.9(2) . . . . ? C1 C2 C3 C4 -77.9(2) . . . . ? C8 C3 C4 C5 0.5(3) . . . . ? C2 C3 C4 C5 178.30(17) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? C4 C5 C6 C7 -0.4(3) . . . . ? C5 C6 C7 C8 -0.1(3) . . . . ? C4 C3 C8 C7 -0.9(3) . . . . ? C2 C3 C8 C7 -178.71(17) . . . . ? C6 C7 C8 C3 0.7(3) . . . . ? N4 C1 C9 C10 -137.44(18) . . . . ? C2 C1 C9 C10 97.3(2) . . . . ? N4 C1 C9 C14 43.4(2) . . . . ? C2 C1 C9 C14 -81.85(19) . . . . ? C14 C9 C10 C11 -0.1(3) . . . . ? C1 C9 C10 C11 -179.31(17) . . . . ? C9 C10 C11 C12 -0.2(3) . . . . ? C10 C11 C12 C13 -0.1(3) . . . . ? C11 C12 C13 C14 0.8(3) . . . . ? C12 C13 C14 C9 -1.2(3) . . . . ? C10 C9 C14 C13 0.8(3) . . . . ? C1 C9 C14 C13 -179.98(18) . . . . ? O1 C15 C16 C17 -146.16(18) . . . . ? N4 C15 C16 C17 33.4(3) . . . . ? O1 C15 C16 C21 29.6(2) . . . . ? N4 C15 C16 C21 -150.89(17) . . . . ? C21 C16 C17 C18 -0.7(3) . . . . ? C15 C16 C17 C18 174.99(17) . . . . ? C16 C17 C18 C19 0.4(3) . . . . ? C17 C18 C19 C20 0.5(3) . . . . ? C17 C18 C19 N5 -178.07(15) . . . . ? C18 C19 C20 C21 -1.1(3) . . . . ? N5 C19 C20 C21 177.45(16) . . . . ? C19 C20 C21 C16 0.8(3) . . . . ? C17 C16 C21 C20 0.1(3) . . . . ? C15 C16 C21 C20 -175.80(17) . . . . ? C3 C2 N1 N2 120.99(18) . . . . ? C1 C2 N1 N2 -118.45(18) . . . . ? C2 N1 N2 N3 -169.7(16) . . . . ? O1 C15 N4 C1 3.5(3) . . . . ? C16 C15 N4 C1 -176.03(15) . . . . ? C9 C1 N4 C15 107.2(2) . . . . ? C2 C1 N4 C15 -127.82(18) . . . . ? C20 C19 N5 O2 -7.3(2) . . . . ? C18 C19 N5 O2 171.30(16) . . . . ? C20 C19 N5 O3 173.14(16) . . . . ? C18 C19 N5 O3 -8.3(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H1N4 O1 0.783(19) 2.19(2) 2.912(2) 154.2(17) 1_455 # END of CIF _database_code_depnum_ccdc_archive 'CCDC 967684' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_RajanBabu1748 _audit_creation_date 2013-08-01T11:13:24-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common RajanBabu1748 _chemical_formula_moiety 'C14 H15 N3 O3 S1' _chemical_formula_sum 'C14 H15 N3 O3 S' _chemical_formula_weight 305.35 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system orthorhombic _space_group_name_H-M_alt Pbca _space_group_name_Hall '-P 2ac 2ab' _space_group_IT_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 7.6612(1) _cell_length_b 13.3624(1) _cell_length_c 28.3524(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2902.49(5) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3707 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'square plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_special_details ;All work was done at 150 K using an Oxford Cryosystems Cryostream Cooler. The data collection strategy was set up to measure a quadrant of reciprocal space with a redundancy factor of 3.5, which means that 90% of these reflections were measured at least 3.5 times. Phi and omega scans with a frame width of 1.0 degree were used. Data integration was done with Denzo, and scaling and merging of the data was done with Scalepack. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.237 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.865 _exptl_absorpt_correction_T_max 0.972 _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.710871E-1 _diffrn_orient_matrix_ub_12 0.109422 _diffrn_orient_matrix_ub_13 -0.33144E-2 _diffrn_orient_matrix_ub_21 -0.323749E-1 _diffrn_orient_matrix_ub_22 0.190723E-1 _diffrn_orient_matrix_ub_23 -0.647199E-1 _diffrn_orient_matrix_ub_31 -0.253419E-1 _diffrn_orient_matrix_ub_32 0.169994E-1 _diffrn_orient_matrix_ub_33 0.176864E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_av_unetI/netI ? _diffrn_reflns_number 48232 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _reflns_number_total 3295 _reflns_number_gt 2508 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ;The hydrogen atom bonded to N(2) was refined isotropically. The rest of the hydrogen atoms were included in the model at calculated positions using a riding model with U(H) = 1.2 * Ueq(bonded atom). Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0381P)^2^+0.8024P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3295 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.053 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0829 _refine_ls_wR_factor_gt 0.0769 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.227 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.042 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.28864(17) 0.67438(10) 0.06649(5) 0.0200(3) Uani 1 1 d . . . H1 H 0.2799 0.7472 0.0586 0.024 Uiso 1 1 calc R . . C2 C 0.31968(18) 0.61907(10) 0.02029(5) 0.0227(3) Uani 1 1 d . . . H2A H 0.2228 0.6335 -0.0018 0.027 Uiso 1 1 calc R . . H2B H 0.3212 0.5461 0.0263 0.027 Uiso 1 1 calc R . . C3 C 0.4924(2) 0.65051(11) -0.00220(5) 0.0259(3) Uani 1 1 d . . . H3A H 0.513 0.6105 -0.031 0.031 Uiso 1 1 calc R . . H3B H 0.4863 0.7219 -0.0114 0.031 Uiso 1 1 calc R . . C4 C 0.64302(19) 0.63500(11) 0.03232(5) 0.0257(3) Uani 1 1 d . . . H4A H 0.6542 0.5629 0.0398 0.031 Uiso 1 1 calc R . . H4B H 0.7535 0.6574 0.0176 0.031 Uiso 1 1 calc R . . C5 C 0.61151(18) 0.69370(11) 0.07755(5) 0.0249(3) Uani 1 1 d . . . H5A H 0.6082 0.7661 0.0702 0.03 Uiso 1 1 calc R . . H5B H 0.7095 0.6819 0.0996 0.03 Uiso 1 1 calc R . . C6 C 0.43994(17) 0.66318(10) 0.10127(4) 0.0205(3) Uani 1 1 d . . . H6 H 0.4485 0.5913 0.1109 0.025 Uiso 1 1 calc R . . C7 C 0.10767(19) 0.51328(12) 0.09572(5) 0.0284(3) Uani 1 1 d . . . C8 C 0.39335(18) 0.68513(10) 0.18685(5) 0.0227(3) Uani 1 1 d . . . C9 C 0.36710(17) 0.75956(10) 0.22623(5) 0.0212(3) Uani 1 1 d . . . C10 C 0.40085(19) 0.72669(10) 0.27184(5) 0.0250(3) Uani 1 1 d . . . H10 H 0.4403 0.6601 0.2769 0.03 Uiso 1 1 calc R . . C11 C 0.37757(19) 0.78989(11) 0.30996(5) 0.0262(3) Uani 1 1 d . . . H11 H 0.4015 0.7677 0.3411 0.031 Uiso 1 1 calc R . . C12 C 0.31873(18) 0.88605(10) 0.30171(5) 0.0225(3) Uani 1 1 d . . . C13 C 0.28230(19) 0.92127(10) 0.25701(5) 0.0248(3) Uani 1 1 d . . . H13 H 0.2407 0.9875 0.2523 0.03 Uiso 1 1 calc R . . C14 C 0.30804(19) 0.85734(10) 0.21920(5) 0.0240(3) Uani 1 1 d . . . H14 H 0.2852 0.8803 0.1881 0.029 Uiso 1 1 calc R . . N1 N 0.1240(2) 0.42822(11) 0.09726(5) 0.0452(4) Uani 1 1 d . . . N2 N 0.41072(16) 0.72354(9) 0.14324(4) 0.0229(3) Uani 1 1 d . . . H2 H 0.404(2) 0.7826(12) 0.1400(5) 0.028(4) Uiso 1 1 d . . . N3 N 0.29193(17) 0.95263(9) 0.34249(4) 0.0294(3) Uani 1 1 d . . . O1 O 0.39886(16) 0.59500(7) 0.19475(4) 0.0362(3) Uani 1 1 d . . . O2 O 0.35134(18) 0.92665(9) 0.38079(4) 0.0445(3) Uani 1 1 d . . . O3 O 0.21068(16) 1.03055(8) 0.33653(4) 0.0390(3) Uani 1 1 d . . . S S 0.07953(4) 0.63824(3) 0.093497(13) 0.02623(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0203(7) 0.0177(6) 0.0222(7) 0.0022(5) 0.0015(5) -0.0005(5) C2 0.0248(7) 0.0236(7) 0.0197(7) -0.0004(6) -0.0020(6) 0.0007(6) C3 0.0296(8) 0.0272(7) 0.0209(7) 0.0008(6) 0.0037(6) 0.0013(6) C4 0.0225(7) 0.0290(8) 0.0255(7) -0.0007(6) 0.0048(6) -0.0001(6) C5 0.0221(7) 0.0272(7) 0.0254(7) -0.0013(6) -0.0016(6) -0.0021(6) C6 0.0244(7) 0.0185(6) 0.0187(7) -0.0009(5) -0.0004(5) 0.0011(5) C7 0.0284(8) 0.0292(8) 0.0274(8) 0.0025(6) 0.0038(6) -0.0046(6) C8 0.0234(7) 0.0228(7) 0.0220(7) 0.0016(6) 0.0014(6) -0.0005(6) C9 0.0194(7) 0.0224(7) 0.0217(7) 0.0005(6) 0.0009(5) -0.0018(6) C10 0.0293(8) 0.0217(7) 0.0240(7) 0.0030(6) 0.0004(6) 0.0015(6) C11 0.0320(8) 0.0296(8) 0.0171(7) 0.0043(6) -0.0023(6) -0.0005(6) C12 0.0223(7) 0.0259(7) 0.0193(7) -0.0027(6) 0.0017(6) -0.0019(6) C13 0.0279(8) 0.0226(7) 0.0240(7) 0.0015(6) 0.0003(6) 0.0031(6) C14 0.0287(8) 0.0264(7) 0.0170(7) 0.0027(6) -0.0010(5) 0.0016(6) N1 0.0568(10) 0.0265(8) 0.0522(10) 0.0065(7) 0.0101(7) -0.0046(7) N2 0.0331(7) 0.0159(6) 0.0197(6) -0.0009(5) 0.0004(5) 0.0005(5) N3 0.0346(7) 0.0309(7) 0.0228(7) -0.0017(5) 0.0031(5) -0.0048(6) O1 0.0627(8) 0.0196(5) 0.0265(6) 0.0024(4) 0.0098(5) 0.0044(5) O2 0.0715(9) 0.0408(7) 0.0212(6) -0.0046(5) -0.0081(6) 0.0010(6) O3 0.0508(7) 0.0335(6) 0.0328(6) -0.0057(5) 0.0065(5) 0.0100(5) S 0.02138(19) 0.02335(19) 0.0340(2) -0.00113(15) 0.00530(15) 0.00084(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.5227(18) . ? C1 C6 1.5291(18) . ? C1 S 1.8402(13) . ? C1 H1 1 . ? C2 C3 1.527(2) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C4 1.527(2) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 C5 1.5227(19) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 C6 1.5317(19) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 N2 1.4550(17) . ? C6 H6 1 . ? C7 N1 1.144(2) . ? C7 S 1.6847(16) . ? C8 O1 1.2258(17) . ? C8 N2 1.3451(17) . ? C8 C9 1.5087(19) . ? C9 C10 1.3901(18) . ? C9 C14 1.3969(19) . ? C10 C11 1.383(2) . ? C10 H10 0.95 . ? C11 C12 1.3815(19) . ? C11 H11 0.95 . ? C12 C13 1.3805(19) . ? C12 N3 1.4733(17) . ? C13 C14 1.3849(19) . ? C13 H13 0.95 . ? C14 H14 0.95 . ? N2 H2 0.796(16) . ? N3 O3 1.2248(16) . ? N3 O2 1.2275(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 112.88(11) . . ? C2 C1 S 111.50(9) . . ? C6 C1 S 111.47(9) . . ? C2 C1 H1 106.9 . . ? C6 C1 H1 106.9 . . ? S C1 H1 106.9 . . ? C1 C2 C3 111.15(11) . . ? C1 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? C1 C2 H2B 109.4 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 108 . . ? C4 C3 C2 110.48(11) . . ? C4 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? C4 C3 H3B 109.6 . . ? C2 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? C5 C4 C3 110.48(12) . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C4 C5 C6 111.63(11) . . ? C4 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? C4 C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 108 . . ? N2 C6 C1 110.89(11) . . ? N2 C6 C5 110.09(11) . . ? C1 C6 C5 109.96(11) . . ? N2 C6 H6 108.6 . . ? C1 C6 H6 108.6 . . ? C5 C6 H6 108.6 . . ? N1 C7 S 178.91(15) . . ? O1 C8 N2 122.64(13) . . ? O1 C8 C9 121.13(12) . . ? N2 C8 C9 116.22(12) . . ? C10 C9 C14 119.24(12) . . ? C10 C9 C8 117.09(12) . . ? C14 C9 C8 123.65(12) . . ? C11 C10 C9 120.66(13) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C10 118.53(12) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C13 C12 C11 122.58(13) . . ? C13 C12 N3 119.10(12) . . ? C11 C12 N3 118.31(12) . . ? C12 C13 C14 118.13(13) . . ? C12 C13 H13 120.9 . . ? C14 C13 H13 120.9 . . ? C13 C14 C9 120.85(12) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? C8 N2 C6 123.75(12) . . ? C8 N2 H2 118.6(11) . . ? C6 N2 H2 117.7(11) . . ? O3 N3 O2 123.44(13) . . ? O3 N3 C12 118.41(12) . . ? O2 N3 C12 118.15(12) . . ? C7 S C1 99.46(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -54.35(15) . . . . ? S C1 C2 C3 179.27(9) . . . . ? C1 C2 C3 C4 55.61(15) . . . . ? C2 C3 C4 C5 -57.65(15) . . . . ? C3 C4 C5 C6 58.10(15) . . . . ? C2 C1 C6 N2 175.49(11) . . . . ? S C1 C6 N2 -58.11(13) . . . . ? C2 C1 C6 C5 53.49(15) . . . . ? S C1 C6 C5 179.90(9) . . . . ? C4 C5 C6 N2 -177.69(11) . . . . ? C4 C5 C6 C1 -55.22(15) . . . . ? O1 C8 C9 C10 18.6(2) . . . . ? N2 C8 C9 C10 -161.18(13) . . . . ? O1 C8 C9 C14 -160.03(14) . . . . ? N2 C8 C9 C14 20.2(2) . . . . ? C14 C9 C10 C11 -0.4(2) . . . . ? C8 C9 C10 C11 -179.07(13) . . . . ? C9 C10 C11 C12 0.5(2) . . . . ? C10 C11 C12 C13 0.1(2) . . . . ? C10 C11 C12 N3 179.21(13) . . . . ? C11 C12 C13 C14 -0.7(2) . . . . ? N3 C12 C13 C14 -179.85(13) . . . . ? C12 C13 C14 C9 0.8(2) . . . . ? C10 C9 C14 C13 -0.3(2) . . . . ? C8 C9 C14 C13 178.31(13) . . . . ? O1 C8 N2 C6 -0.8(2) . . . . ? C9 C8 N2 C6 178.89(12) . . . . ? C1 C6 N2 C8 117.35(14) . . . . ? C5 C6 N2 C8 -120.73(14) . . . . ? C13 C12 N3 O3 12.31(19) . . . . ? C11 C12 N3 O3 -166.87(13) . . . . ? C13 C12 N3 O2 -168.19(14) . . . . ? C11 C12 N3 O2 12.6(2) . . . . ? N1 C7 S C1 -16E1(7) . . . . ? C2 C1 S C7 54.80(11) . . . . ? C6 C1 S C7 -72.35(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 N1 0.796(16) 2.302(17) 3.0415(18) 154.8(15) 7_665 # END of CIF _database_code_depnum_ccdc_archive 'CCDC 967685'